Tetrahydrofuran → [(1,4-Dioxa-spiro[4.5]dec-8-yl)-4-fluorophenylmethyl]-dimethylamine

HRID 1645391Notes

Reaction equation

HRID 1645391 reaction equation
[CH3:1][N:2]([CH:4]([CH:7]1[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH2:8]1)[C:5]#N)[CH3:3].C1COCC1.[F:22][C:23]1[CH:28]=[CH:27]C([Mg]Br)=[CH:25][CH:24]=1.[Cl-].[NH4+]>O>[O:14]1[C:10]2([CH2:15][CH2:16][CH:7]([CH:4]([N:2]([CH3:3])[CH3:1])[C:5]3[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=3)[CH2:8][CH2:9]2)[O:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 57839521Dimethylamino-(1,4-dioxaspiro[4.5]dec-8-yl)-acetonitrileHCID 178418676HCID 178418676, compound

Product 1

HCID 66703550[(1,4-Dioxa-spiro[4.5]dec-8-yl)-4-fluorophenylmethyl]-dimethylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the aminonitrile 4 (19.89 g, 88 mmol) in absol. THF (160 ml) was added dropwise to a 1 M solution of 4-fluorophenylmagnesium bromide in THF (220 ml, 220 mmol) under argon and while cooling with ice and the mixture was stirred at RT for 20 h. The reaction mixture was worked up by adding saturated ammonium chloride solution (100 ml) and water (100 ml) while cooling with ice, and extracting the mixture with diethyl ether (3×100 ml). The organic phase was washed with water and saturated sodium chloride solution, dried (Na2SO4) and concentrated.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice
  3. extractionextracting the mixture with diethyl ether (3×100 ml)
  4. washThe organic phase was washed with water and saturated sodium chloride solution
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-37370c2915d1495e89d471ecf89fe6d6
Source dataset
uspto-grants-2012_02
Patent number
US08124788B2

Reaction notes

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